28924-18-7

Basic information

• Product Name: 1-[3,5-bis(phenylmethoxy)phenyl]-2-bromoethan-1-one
• Synonyms: 1-[3,5-bis(phenylmethoxy)phenyl]-2-bromoethan-1-one;1-[3,5-Bis(phenylmethoxy)phenyl]-2-bromoethanone;3',5'-Bis(benzyloxy)-2-broMo-acetophenone;2-bromo-1-[3,5-bis(phenylmethoxy)phenyl]ethanone
• CAS NO: 28924-18-7
• Molecular Formula: C₂₂H₁₉BrO₃
• Molecular Weight: 411.28846
• EINECS: 249-314-1
• Product Categories: Aromatics
• Mol File: 28924-18-7.mol

Chemical Properties

• Melting Point: 84-86°C
• Boiling Point: 523.8°Cat760mmHg
• Flash Point: 270.6°C
• Appearance: /
• Density: 1.354g/cm³
• Vapor Pressure: 4.56E-11mmHg at 25°C
• Refractive Index: 1.617
• CAS DataBase Reference: 1-[3,5-bis(phenylmethoxy)phenyl]-2-bromoethan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[3,5-bis(phenylmethoxy)phenyl]-2-bromoethan-1-one(28924-18-7)
• EPA Substance Registry System: 1-[3,5-bis(phenylmethoxy)phenyl]-2-bromoethan-1-one(28924-18-7)

Safety Data

• Hazardous Substances Data: 28924-18-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C22H19BrO3/c23-14-22(24)19-11-20(25-15-17-7-3-1-4-8-17)13-21(12-19)26-16-18-9-5-2-6-10-18/h1-13H,14-16H2

Upstream product

• 28924-21-2 3,5-dibenzyloxyacetophenone 
• 52144-91-9 3,5-bis(benzyloxy)diazoacetophenone 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 58605-10-0 methyl 3,5-bis(benzyloxy)benzoate 
• 28917-43-3 3,5-dibenzyloxybenzoic acid 
• 100-44-7 benzyl chloride 
• 51863-60-6 3,5-dihydroxyacetophenone 
• 28917-44-4 3,5-dibenzyloxylbenzoyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 50841-47-9 3,5-dibenzilossi-1-epossietilbenzene 
• 103145-39-7 2-bromo-1-(3,5-bis(benzyloxy)phenyl)ethanol 
• 28924-21-2 3,5-dibenzyloxyacetophenone 
• 103145-34-2 (R)-3’,5’-dibenzyloxyphenylbromohydrin 
• 1026590-20-4 C₃₇H₃₇NO₃ 
• 943962-07-0 (R)-(+)-5-(1-hydroxy-2-phenethylaminoethyl)-1,3-benzenediol 
• 1026184-18-8 C₄₅H₄₅NO₄ 
• 1026647-78-8 C₄₅H₄₅NO₄ 
• 1026431-76-4 C₄₅H₄₅NO₄ 
• 1026431-67-3 C₃₉H₄₁NO₄ 

Relevant articles and documents

Terbutaline sulfate intermediate, preparation method thereof and method for preparing terbutaline sulfate by using same (by machine translation)

The invention discloses a terbutaline sulfate intermediate and a preparation method thereof as well as a method for preparing terbutaline sulfate by using the same, and belongs to the technical field of pharmaceutical chemistry. The invention provides a novel method for preparing terbutaline sulfate which is mild in reaction condition, high in yield and environmentally friendly, and firstly provides a terbutaline sulfate intermediate shown as a formula I; then, a catalyst is used as 10% Pd/C, an alcohol aqueous solution is used as a solvent, and hydrogenation is reduced to obtain the terbutaline II sulfate. The free base hydrochloride or hydrobromide of the formula I is converted into the formula I before hydrogenation reduction, then the terbutaline sulfate is directly obtained after hydrogenation reduction, and the advantages of mild reaction conditions, high product yield, high purity, low production cost and the like are avoided. (by machine translation)

Preparation method of terbutaline sulfate (by machine translation)

The method adopts,hydroxyacetophenone as the starting material 3,5 - to obtain, di 3,5 -benzyloxyacetophenone, 3,5 - dibenzyloxyacetophenone and then generates, DMSO-benzyloxy 3,5 -phenyl,tert-butylamino 1 - [3,5 - ethanol (by hydrogenation debenzil) and sulfuric acid into a salt to obtain dibenzyloxybenzenethanone aldehyde] - 2 - (and then reductive amination with tertiary butylamine.) reaction conditions under, reaction conditions, are avoided, The method disclosed by the invention is cheap and easy to obtain and avoids the use of high-risk highly-toxic agents, by reductive amination . The method disclosed by the invention is low, reaction conditions . The method disclosed by the invention is cheap and easily available. (by machine translation)

Preparation method of high-purity injection-grade terbutaline sulfate

The invention provides a preparation method of high-purity injection-grade terbutaline sulfate. The preparation method is characterized in that 3,5-dibenzyloxyacetophenone is adopted as a raw material, a bromination reaction, a substitution reaction, carbonyl reduction and hydrogenation reduction are conducted, salifying with sulfuric acid is conducted, and the terbutaline sulfate is obtained. A synthetic route is shown in the description.

A method of preparing R-terbutaline

A method of preparing R-terbutaline is disclosed for the first time. According to the method, 3,5-dibenzyloxyacetophenone is adopted as an initial material, is subjected to a bromination reaction, and then reduced by borane-methyl sulfide complex under catalysis by S-methyl-CBS; a product is coupled with N-benzyl-tert-butylamine, and then is hydrogenated to remove benzyl to prepare optically pure R-terbutaline; and the R-terbutaline is salted by utilizing a corresponding acid to prepare a medical salt of the R-terbutaline.

Use of fenoterol and fenoterol analogues in the treatment of glioblastomas and astrocytomas

This disclosure concerns the discovery of the use of fenoterol and (R,R)- and (R,S)-fenoterol analogs for the treatment of a tumor expressing a β2-adrenergic receptor, such as a primary brain tumor, including a glioblastoma or astrocytoma expressing a β2-adrenergic receptor. In one example, the method includes administering to a subject a therapeutically effective amount of fenoterol, a specific fenoterol analog or a combination thereof to reduce one or more symptoms associated with the tumor, thereby treating the tumor in the subject.

UREA COMPOUNDS AND THEIR USE AS FAAH ENZYME INHIBITORS

There is provided a compound having Formula I:(I) wherein: R1 is aryl which is optionally substituted with one or more groups selected from hydroxyl, halogen and C1-4 alkoxy, or R1 is aryl which is substituted with a second aryl group or an aryloxy group, wherein the second aryl group or the aryloxy group is optionally substituted with one or more groups selected from hydroxyl, halogen and C1-4 alkoxy; R2 is C1-4 alkyl; R3 is selected from hydroxyl and OSO2CH3; R4 and R5 are independently selected from hydrogen, hydroxyl and halogen; and n is 0 or 1; or a pharmaceutically acceptable salt thereof; wherein when R3 is hydroxyl and R4 and R5 are not hydroxyl, the optionally substituted aryl group, second aryl group or aryloxy group of R1 is substituted with one or more hydroxyl groups or C1-4 alkoxy groups, or wherein when R3 is hydroxyl, one of R4 and R5 is hydroxyl, provided that the compound is not N-(1-benzylpiperidin-4-yl)-4-(3,4-dihydroxyphenyl)-N-methyl-1H-imidazole-1-carboxamide hydrobromide. The compound may be used as an inhibitor of fatty acid amide hydrolase.

PREPARATION OF (R,R)-FENOTEROL AND (R,R)- OR (R,S)-FENOTEROL ANALOGUES AND THEIR USE IN TREATING CONGESTIVE HEART FAILURE

This disclosure concerns the discovery of (R,R)- and (R,S)-fenoterol analogues which are highly effective at binding β2-adrenergic receptors. Exemplary chemical structures for these analogues are provided. Also provided are pharmaceutical compositions including the disclosed (R,R)-fenoterol and fenoterol analogues, and methods of using such compounds and compositions for the treatment of cardiac disorders such as congestive heart failure and pulmonary disorders such as asthma or chronic obstructive pulmonary disease.

Comparative molecular field analysis of the binding of the stereoisomers of fenoterol and fenoterol derivatives to the β2 adrenergic receptor

Stereoisomers of fenoterol and six fenoterol derivatives have been synthesized and their binding affinities for the β2 adrenergic receptor (Kiβ2-AR), the subtype selectivity relative to the β1-AR (Kiβ1-AR/K iβ2-AR) and their functional activities were determined. Of the 26 compounds synthesized in the study, submicromolar binding affinities were observed for (R,R)-fenoterol, the (R,R)-isomer of the p-methoxy, and (R,R)- and (R,S)-isomers of 1-naphthyl derivatives and all of these compounds were active at submicromolar concentrations in cardiomyocyte contractility tests. The Kiβ1-AR/K iβ2-AR ratios were >40 for (R,R)-fenoterol and the (R,R)-p-methoxy and (R,S)-1-naphthyl derivatives and 14 for the (R,R)-1-napthyl derivative. The binding data was analyzed using comparative molecular field analysis (CoMFA), and the resulting model indicated that the fenoterol derivatives interacted with two separate binding sites and one steric restricted site on the pseudo-receptor and that the chirality of the second stereogenic center affected Kiβ2 and subtype selectivity.

Compounds for the treatment of diseases

The invention relates to compounds of formula (1) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. The compounds according to the present invention are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions.

Synthesis of [18F]-Fluoroethylfenoterol for Imaging &β2 Receptor Status in Lung In Vivo

5-(2-{2-[4-(2-[18F]fluoroethoxy)-phenyl]-1-methyl-ethylamino}-1-hydroxy-ethyl)-benzene-1,3-diol ([18F]fluoroethylfenoterol) was synthesised from 4-(2-{benzyl-[2-(3,5-bis-benzyloxy-phenyl)-2-hydroxy-ethyl]-amino}-propyl)-phenol using 2-[18F]fluoroethyltosylate (92 percent RCY) followed by reductive cleavage of the benzyl protecting groups. Preliminary in vitro tests showed [19F]fluoroethylfenoterol to be as potent in relaxation of lung tissue as fenoterol itself.